Day: November 22, 2022

Efficient Delivery of Cell Impermeable Phosphopeptides by a Cyclic Peptide Amphiphile Containing Tryptophan and Arginine was written by Nasrolahi Shirazi, Amir;Tiwari, Rakesh Kumar;Oh, Donghoon;Banerjee, Antara;Yadav, Arpita;Parang, Keykavous. And the article was included in Molecular Pharmaceutics in 2013.Related Products of 156311-83-0 The following contents are mentioned in the article:

Phosphopeptides are valuable reagent probes for studying protein-protein and protein-ligand interactions. The cellular delivery of phosphopeptides is challenging because of the presence of the neg. charged phosphate group. The cellular uptake of a number of fluorescent-labeled phosphopeptides, including F’-GpYLPQTV, F’-NEpYTARQ, F’-AEEEIYGEFEAKKKK, F’-PEpYLGLD, F’-pYVNVQN-NH₂, and F’-GpYEEI (F’ = fluorescein), was evaluated in the presence or absence of a [WR]₄, a cyclic peptide containing alternative arginine (R) and tryptophan (W) residues, in human leukemia cells (CCRF-CEM) after 2 h incubation using flow cytometry. [WR]₄ improved significantly the cellular uptake of all phosphopeptides. PEpYLGLD is a sequence that mimics the pTyr1246 of ErbB2 that is responsible for binding to the Chk SH2 domain. The cellular uptake of F’-PEpYLGLD was enhanced dramatically by 27-fold in the presence of [WR]₄ and was found to be time-dependent. Confocal microscopy of a mixture of F’-PEpYLGLD and [WR]₄ in live cells exhibited intracellular localization and significantly higher cellular uptake compared to that of F’-PEpYLGLD alone. Transmission electron microscopy (TEM) and isothermal calorimetry (ITC) were used to study the interaction of PEpYLGLD and [WR]₄. TEM results showed that the mixture of PEpYLGLD and [WR]₄ formed noncircular nanosized structures with width and height of 125 and 60 nm, resp. ITC binding studies confirmed the interaction between [WR]₄ and PEpYLGLD. The binding isotherm curves, derived from sequential binding models, showed an exothermic interaction driven by entropy. These studies suggest that amphiphilic peptide [WR]₄ can be used as a cellular delivery tool of cell-impermeable neg. charged phosphopeptides. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Related Products of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Related Products of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Investigation on condensing agents for phosphinate ester formation with nucleoside 5′-hydroxyl functions was written by Winqvist, Anna;Stroemberg, Roger. And the article was included in European Journal of Organic Chemistry in 2008.Electric Literature of C17H27F6N7OP2 The following contents are mentioned in the article:

Condensation of a uridine 3′-deoxy-3′-C-methylenephosphinate with thymidine and guanosine derivatives to form methylenephosphinate esters was investigated. A number of different condensing agents were compared, and these include pivaloyl chloride, triisopropylbenzenesulfonyl chloride (TPS-Cl), phosphonium and uronium derivatives, numerous chlorophosphates and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (OXP). The phosphonium derivatives gave slow condensations or oxidative side reactions (hydroxybenzotriazole derivatives) during preactivation of the methylenephosphinate. Pivaloyl chloride gave long coupling times, and competing 5′-O-pivaloylation was detected. TPS-Cl gave rapid condensation but also rapid oxidation of the product. Most chlorophosphates gave competing 5′-O-phosphorylation of the nucleoside component, as well as base phosphorylation. However, 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane (DMOCP) gave a rather efficient formation of dinucleoside methylenephosphinates at a decent rate. However, O⁶-protection of guanines could become necessary with this reagent, since upon extended reaction time traces of O⁶-phosphorylation were detected even with a low concentration (60 mM) of DMOCP (2 equivalent to phosphinate). Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (OXP) can, unlike DMOCP, be used in nearly equimolar amounts to phosphinate. Under such conditions OXP gives virtually quant. condensation at a rate comparable to that of 2 equivalent of DMOCP and with no side reactions detected. Any decomposition of OXP-preactivated phosphinate could also not be detected. Nucleophilic catalysts, more powerful than pyridine (N-methylimidazole, iodide and 4-methoxypyridine), accelerated the reactions with OXP, but preactivation in the absence of the 5′-OH component led to decomposition of the activated phosphinate. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Electric Literature of C17H27F6N7OP2).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Electric Literature of C17H27F6N7OP2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Global optimization of conformational constraint on non-phosphorylated cyclic peptide antagonists of the Grb2-SH2 domain was written by Long, Ya-Qiu;Lung, Feng-Di T.;Roller, Peter P.. And the article was included in Bioorganic & Medicinal Chemistry in 2003.Synthetic Route of C17H27F6N7OP2 The following contents are mentioned in the article:

Following our earlier work on a phage library derived non-phosphorylated thioether-cyclized peptide inhibitor of Grb2 SH2 domain, a series of small peptide analogs with various cyclization linkage or various ring size were designed and synthesized and evaluated to investigate the optimal conformational constraint for this novel Grb2-SH2 blocker. Our previous SAR studies have indicated that constrained conformation as well as all amino acids except Leu² and Gly⁷ in this lead peptide, cyclo(CH₂CO-Glu¹-Leu-Tyr-Glu-Asn-Val-Gly-Met-Tyr-Cys¹⁰)-amide (termed G1TE), was necessary for sustenance of the biol. activity. In this study, in an effort to derive potent and bioavailable Grb2-SH2 inhibitor with minimal sequence, we undertook a systematic conformational study on this non-phosphorylated cyclic ligand by optimizing the ring linkage, ring configuration and ring size. The polarity and configuration of the cyclization linkage were implicated important in assuming the active conformation. Changing the flexible thioether linkage in G1TE into the relatively rigid sulfoxide linkage secured a 4-fold increase in potency (4, IC₅₀ = 6.5 μM). However, open chain, shortening or expanding the ring size led to a marked loss of inhibitory activity. Significantly, the introduction of ω-amino carboxylic acid linker in place of three C-terminal amino acids in G1TE can remarkably recover the apparently favorable conformation, which is otherwise lost because of the reduced ring size. This modification, combined with favorable substitutions of Gla for Glu¹ and Adi for Glu⁴ in the resulting six-residue cyclic peptide, afforded peptide, with an almost equal potency ,( IC₅₀ = 23.3 μM) relative to G1TE. Moreover, the lipophilic chain in ω-amino carboxylic acid may confer better cell membrane permeability to the peptide. These newly developed G1TE analogs with smaller ring size and less peptide character but equal potency can serve as templates to derive potent and specific non-phosphorylated Grb2-SH2 antagonists. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Synthetic Route of C17H27F6N7OP2).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.Synthetic Route of C17H27F6N7OP2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthesis of Highly Functionalized Polycyclic Quinoxaline Derivatives Using Visible-Light Photoredox Catalysis was written by He, Zhi;Bae, Minwoo;Wu, Jie;Jamison, Timothy F.. And the article was included in Angewandte Chemie, International Edition in 2014.Application In Synthesis of 2-(1,2,4-Triazol-1-yl)aniline The following contents are mentioned in the article:

A mild and facile method for preparing highly functionalized pyrrolo[1,2-a]quinoxalines and other nitrogen-rich heterocycles, each containing a quinoxaline core or an analog thereof, has been developed. The novel method features a visible-light-induced decarboxylation and radical coupling of ortho-substituted aryl isocyanides and radicals generated from phenyliodine(III) dicarboxylate reagents and exhibits excellent functional group compatibility. A wide range of quinoxaline heterocycles have been prepared Finally, a telescoped preparation of these polycyclic compounds by integration of the in-line isocyanide formation and photochem. cyclization has been established in a three-step continuous-flow system. The title compounds thus formed included derivatives of imidazo[1,2-a]quinoxaline, pyrrolo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, benzimidazo[1,2-a]quinoxaline, pyrazolo[1,5-a]quinoxaline, [1,2,4]triazolo[1,5-a]quinoxaline, [1,2,3]triazolo[1,5-a]quinoxaline, tetrazolo[1,5-a]quinoxaline, pyrido[3,2-e][1,2,4]triazolo[1,5a]pyrazine. Under optimized conditions the synthesis of the target compounds was achieved using tris[2-(2-pyridinyl-κN)phenyl-κC]iridium [i.e., fac-Ir(ppy)₃, photoredox catalyst] as a catalyst. Starting materials included bis(benzoato-κO)phenyliodine and bis(acetato-κO)phenyliodine. Key intermediates included isocyanides (isonitriles), such as 1-(2-isocyanophenyl)pyrrole, 1-(2-isocyanophenyl)-1H-indole and similar azole derivatives Reactants included carboxylic acids, such as benzenepropanoic acid, cyclohexaneacetic acid, pentanedioic acid 1-Me ester, (4S)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid, 10-undecenoic acid (fatty acid), 5-pentynoic acid. Amino acids included N-[(1,1-dimethylethoxy)carbonyl]-β-alanine, N-[(1,1-dimethylethoxy)carbonyl]-L-aspartic acid ester., N-[(1,1-dimethylethoxy)carbonyl]-L-glutamic acid ester. (3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-oic acid (cholalic acid) and (3α,5β)-3-(hydroxy)cholan-24-oic acid (lithocholic acid, bile acid) were also used as reactants. This study involved multiple reactions and reactants, such as 2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1Application In Synthesis of 2-(1,2,4-Triazol-1-yl)aniline).

2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1) belongs to triazole derivatives. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Application In Synthesis of 2-(1,2,4-Triazol-1-yl)aniline

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Functionalization of Intact Trimetaphosphate: A Triphosphorylating Reagent for C, N, and O Nucleophiles was written by Shepard, Scott M.;Cummins, Christopher C.. And the article was included in Journal of the American Chemical Society in 2019.Formula: C17H27F6N7OP2 The following contents are mentioned in the article:

Trimetaphosphate (TriMP, [P₃O₉]^3-) reacts with PyAOP ([(H₈C₄N)₃PON₄C₅H₃][PF₆]) to yield an activated TriMP, [P₃O₉P(NC₄H₈)₃]^– (1), incorporating a phosphonium moiety. Anion 1 is isolated as its bis(triphenylphosphine)iminium (PPN) salt in 70% yield and phosphorylates nucleophiles with elimination of phosphoramide OP(NC₄H₈)₃. Treatment of 1 with amines HNR¹R² generates [P₃O₈NR¹R²]^2- (2a: R¹ = R² = Et; 2b: R¹ = H, R² = ^tBu) in greater than 70% yield as mixed PPN and alkyl ammonium salts. Treatment of 1 with primary alcs. in the presence of a tertiary amine base results in salts of intact TriMP alkyl esters [P₃O₉R]^2- (3a: R = Me; 3b: R = Et) in greater than 60% isolated yield. Reaction of 1 with [PPN][H₂PO₄] provides orthophosphoryl TriMP (4, [P₄O₁₂H₂]^2-) in 40% yield as the PPN salt. Treatment of 1 with Wittig reagent H₂CPPh₃ (4 equiv) provides phosphorus ylide [P₃O₈CHPPh₃]^2- (5) in 61% yield as a mixed salt. Ylide 5 reacts with water to provide [P₃O₈Me]^2-(6) and with aldehydes to give olefins [P₃O₈CHCHR]^2- (7a: R = H; 7b: R = 4-C₆H₄Br), products in which one TriMP oxygen is replaced by a phosphonate P-C linkage. Treatment of intact TriMP derivatives 2a, 2b, 3a, and 7a with aqueous tetrabutylammonium hydroxide results in ring opening to linear triphosphate derivatives X-ray crystal structures are provided for salts of 1, 2a, 3a, and 4. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Formula: C17H27F6N7OP2).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeFormula: C17H27F6N7OP2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives was written by Basava, Vikram;Yang, Lijia;Pradhan, Padmanava;Lakshman, Mahesh K.. And the article was included in Organic & Biomolecular Chemistry in 2016.Reference of 156311-83-0 The following contents are mentioned in the article:

Reaction of amide bonds in t-butyldimethylsilyl-protected inosine, 2′-deoxyinosine, guanosine, 2′-deoxyguanosine, and 2-phenylinosine with com. available peptide-coupling agents (benzotriazol-1H-yloxy)tris(dimethylaminophosphonium) hexafluorophosphate (BOP), (6-chloro-benzotriazol-1H-yloxy)trispyrrolidinophosphonium hexafluorophosphate (PyClocK), and (7-azabenzotriazol-1H-yloxy)trispyrrolidinophosphonium hexafluorophospate (PyAOP) gave the corresponding O⁶-(benzotriazol-1-yl) nucleoside analogs containing a C-O-N bond. Upon exposure to bis(pinacolato)diboron and base, the O⁶-(benzotriazol-1-yl) and O⁶-(6-chlorobenzotriazol-1-yl) purine nucleoside derivatives obtained from BOP and PyClocK, resp., underwent N-O bond reduction and C-N bond formation, leading to the corresponding C6 benzotriazolyl purine nucleoside analogs. In contrast, the 7-azabenzotriazolyloxy purine nucleoside derivatives did not undergo efficient deoxygenation, but gave unsym. nucleoside dimers instead. This is consistent with a prior report on the slow reduction of 1-hydroxy-1H-4-aza and 1-hydroxy-1H-7-azabenzotriazoles. Because of the limited number of com. benzotriazole-based peptide coupling agents, and to show the applicability of the method when such coupling agents are unavailable, 1-hydroxy-1H-5,6-dichlorobenzotriazole was synthesized. Using this compound, silyl-protected inosine and 2′-deoxyinosine were converted to the O⁶-(5,6-dichlorobenzotriazol-1-yl) derivatives via in situ amide activation with PyBroP. The O⁶-(5,6-dichlorobenzotriazol-1-yl) purine nucleosides so obtained also underwent smooth reduction to afford the corresponding C6 5,6-dichlorobenzotriazolyl purine nucleoside derivatives A total of 13 examples were studied with successful reactions occurring in 11 cases (the azabenzotriazole derivatives, mentioned above, being the only unreactive entities). To understand whether these reactions are intra or intermol. processes, a crossover experiment was conducted. The results of this experiment as well as those from reactions conducted in the absence of bis(pinacolato)diboron and in the presence of water indicate that detachment of the benzotriazoloxy group from the nucleoside likely occurs, followed by reduction, and re-attachment of the ensuing benzotriazole, leading to products. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Reference of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.Reference of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics